Oakland Vacations from $508
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Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Stay Pittsburgh
Downtown Pittsburgh
$887
per person
Nov 25 - Nov 28
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
8/10 Very Good! (325 reviews)
Apartment was on a very busy street next to a 24 hr store and had a lot of people just standing around on the corner all day and night. Not the safest spot after dark. You could hear everything on the street all night, so hard to fall asleep. Building and hall smelled like weed but the apartment was fine. I texted the number that gave me the code and they said they would check the floor, address the issue and keep me posted. Never heard back from them. No thrills but didn’t expect any given the cost. Parking was supposed to be $25/day with in and out privileges in the assigned parking lot but there was never an attendant there so no in and out and charged $30/day.
Reviewed on Sep 20, 2026
Oakmont Inn
Plum
$723
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
10/10 Exceptional! (38 reviews)
From the minute we arrived to the minute we checked out, an amazing stay, very clean, beds comfortable, convenient location. Great space downstairs for family, gym, and breakfast each morning was wonderful. Will stay here again and recommend to friends and family
Reviewed on Jul 5, 2026
Villagio Boutique Hotel
North Side
$667
per person
Oct 31 - Nov 3
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
9.4/10 Exceptional! (150 reviews)
The room was clean and comfortable aside from being super charming. The neighborhood is amazing and the food at the restaurant is fabulous!
Reviewed on Sep 20, 2026
Traveler's Rest Hotel
South Side Flats
$645
per person
Oct 31 - Nov 3
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
9.6/10 Exceptional! (118 reviews)
Very clean, owners were very nice and friendly, great place to stay, especially if you are going to watch the Steelers!
Reviewed on Sep 18, 2026
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
North Shore
2 out of top 10 points of interest in this area
Heinz Field, PNC Park, and The Andy Warhol Museum await in this vibrant area, connected to Downtown Pittsburgh by the iconic Roberto Clemente, Andy Warhol, and Rachel Carson Bridges. Enjoy easy access to two light rail stations.
Strip District
Brimming with specialty shops, unique boutiques, and ethnic food purveyors, the Strip District offers a lively atmosphere with art studios, antique dealers, and the historic St. Stanislaus Kostka Church. Enjoy open-air markets and vibrant nightlife during summer months.
Shadyside
Victorian mansions and modern apartments create a diverse residential atmosphere. Explore upscale stores on Walnut Street, dine at local eateries like Pamela's Diner, and easily walk between the three business corridors. Public transportation is accessible.
North Side
1 out of top 10 points of interest in this area
If you're spending time in North Side, check out sights like Acrisure Stadium or PNC Park and hop on the metro to see more the city at North Side Station or Allegheny Station.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
$155 nightly
$177 total
Oct 7 - Oct 8
Total with taxes and fees
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive Pittsburgh PA
Fully refundableReserve now, pay when you stay
$131 nightly
$149 total
Oct 21 - Oct 22
Total with taxes and fees
8.6/10 Excellent! (1,006 reviews)
"Excellent vibes. Kind, friendly staff. Would recommend"
Reviewed on Sep 21, 2026
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard Pittsburgh PA
Fully refundableReserve now, pay when you stay
$251 nightly
$286 total
Oct 22 - Oct 23
Total with taxes and fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Oakland attractions
Carnegie Museum of Natural History
9.2/10 (58 reviews)
From rare jaguars to geological marvels and ancient fossils, you’ll find it all at this Pittsburgh institution, one of the country’s largest natural history museums.
Carnegie Museum of Art
9.8/10 (7 reviews)
If you like your art with a modern twist, you’re in for a treat at this exceptional museum, which also features impressive furniture and architecture galleries.
Heinz Memorial Chapel
Hosting about 1,000 events per year, this non-sectarian chapel welcomes all and frequently hosts weddings, lectures and concerts as well as religious services.
Cathedral of Learning
9.6/10 (184 reviews)
Take an audio tour and admire the majestic Commons Room and Nationality Rooms in one of the world’s tallest Gothic buildings.
Soldiers and Sailors Memorial Hall and Museum
10.0/10 (1 review)
You can spend an afternoon browsing the exhibits at Soldiers and Sailors Memorial Hall and Museum during your trip to Pittsburgh. Attend a sporting event or visit the shops in this family-friendly area.
Petersen Events Center
10.0/10 (3 reviews)
Catch an event at Petersen Events Center during your trip to Pittsburgh. Amble around this vibrant area's riverfront or attend a sporting event.
Carnegie Library of Pittsburgh
8.6/10 (7 reviews)
Carnegie Library of Pittsburgh is just one of the places to see in Pittsburgh, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Pittsburgh Playhouse
You can make plans for a show at Pittsburgh Playhouse during your trip to Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
Things to do
Pittsburgh: Museum of Illusions Entrance Ticket
$29
per adult
94% of travellers recommend
Black & Gold Pittsburgh History Tour for Sports Fans
$33
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
$13
per adult
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- Visit Downtown Pittsburgh
- Schenley Park
- Carnegie Museum of Art
- Strip District Vacations
- Cathedral of Learning
- Pittsburgh Vacations
- Carnegie Mellon University
- North Shore Vacations
- National Aviary
- Acrisure Stadium
- Carnegie Library of Pittsburgh
- Byham Theater
- Carnegie Science Center
- Grandview Overlook
- Andy Warhol Bridge
- Children's Museum of Pittsburgh
- Monongahela Incline
- Senator John Heinz Regional History Centre
- Lighthouse ArtSpace Pittsburgh
- Visit Pittsburgh
- Duquesne Incline
- University of Pittsburgh
- Phipps Conservatory
- Ppg Paints Arena
- Kennywood
- Where to stay in Pittsburgh
- Roberto Clemente Bridge
- Andy Warhol Museum
- Petersen Events Center
- Point State Park
- The Nationality Rooms
- David L Lawrence Convention Center
- U.s. Steel Tower
- Heinz Memorial Chapel
- Soldiers and Sailors Memorial Hall and Museum
- Market Square
- Pnc Park
- Photo Antiquities Museum of Photographic History
- Carnegie Museum of Natural History
- Rachel Carson Bridge
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.